Global Patent Index - EP 3037405 A1

EP 3037405 A1 20160629 - 3-ACYLOXYMETHYL-3-BUTENYL CARBOXYLATE COMPOUND AND METHOD FOR PRODUCING 4-ALKYL-3-METHYLENEBUTYL CARBOXYLATE

Title (en)

3-ACYLOXYMETHYL-3-BUTENYL CARBOXYLATE COMPOUND AND METHOD FOR PRODUCING 4-ALKYL-3-METHYLENEBUTYL CARBOXYLATE

Title (de)

3-ACYLOXYMETHYL-3-BUTENYL-CARBONSÄUREESTER-VERBINDUNG UND VERFAHREN ZUR HERSTELLUNG VON 4-ALKYL-3-METHYLENEBUTYL-CARBOXYLAT

Title (fr)

COMPOSÉ DE CARBOXYLATE 3-ACYLOXYMÉTHYL-3-BUTÉNYLE ET PROCÉDÉ DE PRODUCTION D'UN CARBOXYLATE 4-ALKYL-3-MÉTHYLÈNEBUTYLE

Publication

EP 3037405 A1 20160629 (EN)

Application

EP 15200346 A 20151216

Priority

JP 2014262614 A 20141225

Abstract (en)

Provided is a simple, selective and efficient method for producing 4-alkyl-3-methylenebutyl carboxylates such as 7-methyl-3-methylene-7-octenyl propionate. More specifically provided is a method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, the method comprising a diacyloxylation step of subjecting a 4-halo-2-halomethyl-1-butene compound (6) to diacyloxylation to obtain a 3-acyloxymethyl-3-butenyl carboxylate compound (3), and a coupling step of subjecting the 3-acyloxymethyl-3-butenyl carboxylate compound (3) to a coupling reaction with an organometallic reagent (4) to obtain the 4-alkyl-3-methylenebutyl carboxylate compound (5).

IPC 8 full level

C07C 67/30 (2006.01); C07C 67/32 (2006.01); C07C 69/52 (2006.01); C07C 69/533 (2006.01); C07C 69/593 (2006.01)

CPC (source: CN EP US)

C07C 17/358 (2013.01 - CN); C07C 21/14 (2013.01 - CN); C07C 67/11 (2013.01 - CN EP US); C07C 67/28 (2013.01 - CN); C07C 67/293 (2013.01 - EP US); C07C 67/297 (2013.01 - US); C07C 69/003 (2013.01 - EP US); C07C 69/007 (2013.01 - CN); C07C 69/02 (2013.01 - US); C07C 69/24 (2013.01 - CN); C07C 69/28 (2013.01 - CN EP US); C07C 69/34 (2013.01 - US)

Citation (applicant)

  • GIESELMANN ET AL., J. CHEM. ECOL., vol. 5, 1979, pages 891
  • ANDERSON ET AL., J. CHEM. ECOL., vol. 5, 1979, pages 919
  • WEILER ET AL., CAN. J. CHEM., vol. 71, 1993, pages 1955
  • WEEDEN ET AL., TET. LETT., vol. 27, 1986, pages 5555
  • ZHANG ET AL., CHINESE CHEMICAL LETTERS, vol. 2, 1991, pages 611
  • HUAXUE TONGBAO, vol. 40, 1994
  • CHONG ET AL., J. ORG. CHEM., vol. 66, 2001, pages 8248
  • VESELOVSKII ET AL., IZVESTIYA AKADEMII NAUK SSSR, SERIYA KHIMICHESKAYA, vol. 3, 1990, pages 513
  • KULINKOVICH, SYNTHESIS, 2005, pages 1713

Citation (search report)

  • [X] PATRIZIA FERRABOSCHI ET AL: "Regio- and enantioselectivity of Pseudomonas cepacia lipase in the transesterification of 2-substituted-1,4-butanediols", TETRAHEDRON ASYMMETRY, vol. 5, no. 4, 1994, OXFORD, GB, pages 691 - 698, XP055266563, ISSN: 0957-4166, DOI: 10.1016/0957-4166(94)80031-6
  • [X] PETER A. WADE ET AL: "Thermolytic rearrangements of 1,1-cyclopropanedimethanol disulfonates: cyclopropylcarbinyl cations revisited", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 58, no. 11, 1993, US, pages 3140 - 3147, XP055266567, ISSN: 0022-3263, DOI: 10.1021/jo00063a039
  • [X] WILLIAM J. BAILEY, W. GRAHAM CARPENTER, MATTHEW E. HERMES: "Pyrolysis of Esters. XXI. 2-Hydroxymethyl-1,2-butadiene", JOURNAL OF ORGANIC CHEMISTRY, 1962, pages 1975 - 1978, XP002756744, DOI: 10.1021/jo01053a012
  • [XA] TABUCHI H ET AL: "Total synthesis of alternaric acid", TETRAHEDRON LETTERS, PERGAMON, GB, vol. 34, no. 14, 2 April 1993 (1993-04-02), pages 2327 - 2330, XP026672405, ISSN: 0040-4039, [retrieved on 19930402], DOI: 10.1016/S0040-4039(00)77605-2
  • [A] VESELOVSKII, V.V. ET AL.: "Synthesis of alpha-Myrcenol Acetate and Propionate from Isobutenylcarbinol", BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR, DIVISION OF CHEMICAL SCIENCE (ENGLISH TRANSLATION), vol. 39, no. 3.1, 1990, pages 513 - 516, XP002756745
  • [A] LI ET AL: "Approaches to selective isoprenologation via reactions of (eta<3>-allyl)Fe(CO)<+>4 with allyl nucleophiles", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 402, no. 1, 22 January 1991 (1991-01-22), pages 105 - 112, XP022057713, ISSN: 0022-328X

Designated contracting state (EPC)

AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

Designated extension state (EPC)

BA ME

DOCDB simple family (publication)

EP 3037405 A1 20160629; EP 3037405 B1 20191030; CN 105732372 A 20160706; CN 105732372 B 20230502; ES 2760258 T3 20200513; JP 2016121107 A 20160707; JP 6249938 B2 20171220; US 2016185707 A1 20160630; US 9499468 B2 20161122

DOCDB simple family (application)

EP 15200346 A 20151216; CN 201510996938 A 20151225; ES 15200346 T 20151216; JP 2014262614 A 20141225; US 201514974104 A 20151218